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Volumn 60, Issue 5, 2002, Pages 283-291

Fast and efficient peptide bond formation using bis-[α,α-bis(trifluoromethyl)-benzyloxy]diphenylsulfur. Part I

Author keywords

Amide; Chiral phase HPLC; Coupling agent; HATU; HBTU; Peptide; Racemization; Sulfurane; Synthesis

Indexed keywords

AMIDE; BENZOYLPHENYLALANINE; BIS[ALPHA,ALPHA BIS(TRIFLUOROMETHYL)BENZYLOXY]DIPHENYLSULFUR; ESTER; PEPTIDE; PHENYLALANINE DERIVATIVE; PHENYLALANINE ETHYL ESTER; SULFUR DERIVATIVE; SULFURANE DERIVATIVE; UNCLASSIFIED DRUG; BIS (ALPHA,ALPHA BIS(TRIFLUOROMETHYL) BENZYLOXY)DIPHENYLSULFUR; BIS-(ALPHA,ALPHA-BIS(TRIFLUOROMETHYL)-BENZYLOXY)DIPHENYLSULFUR;

EID: 0036830213     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2002.21015.x     Document Type: Article
Times cited : (4)

References (47)
  • 1
    • 0344117821 scopus 로고    scopus 로고
    • Recent developments and applications of liquid-phase strategies in organic synthesis
    • Wentworth, P. Jr (1999) Recent developments and applications of liquid-phase strategies in organic synthesis. Trends Biotechnol. 17, 448-452.
    • (1999) Trends Biotechnol. , vol.17 , pp. 448-452
    • Wentworth P., Jr.1
  • 2
    • 0033402902 scopus 로고    scopus 로고
    • 9-Fluorenylmethyloxycarbonyl/tbutyl-based convergent protein synthesis
    • Barlos, K. & Gatos, D. (1999) 9-Fluorenylmethyloxycarbonyl/tbutyl-based convergent protein synthesis. Biopolymers 51, 266-278.
    • (1999) Biopolymers , vol.51 , pp. 266-278
    • Barlos, K.1    Gatos, D.2
  • 4
    • 0001217978 scopus 로고
    • Intramolecular addition of amines to chiral vinyl sulfoxides. Total synthesis of (R)-(+)-canadine
    • Pyne, S.G. (1987) Intramolecular addition of amines to chiral vinyl sulfoxides. Total synthesis of (R)-(+)-canadine. Tetrahedron Lett. 28, 4737-4740.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4737-4740
    • Pyne, S.G.1
  • 5
    • 0005227674 scopus 로고
    • New synthesis of long-chain acetylenic acids and some attempts to prepare pure cis-olefinic acids
    • Ames, D.E. & Islip, P.J. (1961) New synthesis of long-chain acetylenic acids and some attempts to prepare pure cis-olefinic acids. J. Chem. Soc. 351-356.
    • (1961) J. Chem. Soc. , pp. 351-356
    • Ames, D.E.1    Islip, P.J.2
  • 8
    • 0033607452 scopus 로고    scopus 로고
    • 2-Mercaptopyridone 1-oxide-based uronium salts: New peptide coupling reagents
    • Bailén, M.A., Chinchilla, R., Dodsworth, D. & Nájera, C. (1999) 2-Mercaptopyridone 1-oxide-based uronium salts: New peptide coupling reagents. J. Org. Chem. 64, 8936-8939.
    • (1999) J. Org. Chem. , vol.64 , pp. 8936-8939
    • Bailén, M.A.1    Chinchilla, R.2    Dodsworth, D.3    Nájera, C.4
  • 9
    • 0014704672 scopus 로고
    • Eine neue methode zur synthese von peptiden: Aktivierung der carboxylgruppe mit dicyclohexylcarbodiimid unter zusatz von 1-hydroxy-benzotriazolen
    • König, W. & Geiger, R. (1970) Eine neue methode zur synthese von peptiden: Aktivierung der carboxylgruppe mit dicyclohexylcarbodiimid unter zusatz von 1-hydroxy-benzotriazolen. Chem. Ber. 103, 788-798.
    • (1970) Chem. Ber. , vol.103 , pp. 788-798
    • König, W.1    Geiger, R.2
  • 10
    • 49349126081 scopus 로고
    • L'hexafluorophosphate de o-benzotriazolyl-n,n-tetramethyluronium: Un reactif de couplage peptidique nouveau et efficace
    • Dourtoglou, V., Ziegler, J.C. & Gross, B. (1978) L'hexafluorophosphate de o-benzotriazolyl-n,n-tetramethyluronium: Un reactif de couplage peptidique nouveau et efficace. Tetrahedron Lett. 19, 1269-1272.
    • (1978) Tetrahedron Lett. , vol.19 , pp. 1269-1272
    • Dourtoglou, V.1    Ziegler, J.C.2    Gross, B.3
  • 11
    • 0000597775 scopus 로고
    • The reaction of hexamethyl phosphoric triamide (HMPT) with phosphoryl chloride: A reexamination. Application to a novel preparation of BOP reagent for peptide coupling
    • Dormoy, J.R. & Castro, B. (1979) The reaction of hexamethyl phosphoric triamide (HMPT) with phosphoryl chloride: A reexamination. Application to a novel preparation of BOP reagent for peptide coupling. Tetrahedron Lett. 20, 3321-3322.
    • (1979) Tetrahedron Lett. , vol.20 , pp. 3321-3322
    • Dormoy, J.R.1    Castro, B.2
  • 12
    • 0029041801 scopus 로고
    • Improved syntheses of peptide coupling reagents BOP and PyBOP using triphosgene
    • Rivero, A., Somanathan, R. & Hellberg, L.H. (1995) Improved syntheses of peptide coupling reagents BOP and PyBOP using triphosgene. Synth. Commun. 24, 2185-2188.
    • (1995) Synth. Commun. , vol.24 , pp. 2185-2188
    • Rivero, A.1    Somanathan, R.2    Hellberg, L.H.3
  • 13
    • 0033617325 scopus 로고    scopus 로고
    • BOMI - A novel peptide coupling agent
    • Li, P. & Xu, J.C. (1999) BOMI - A novel peptide coupling agent. Tetrahedron Lett. 40, 3605-3608.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3605-3608
    • Li, P.1    Xu, J.C.2
  • 14
    • 0342656979 scopus 로고    scopus 로고
    • Total synthesis of cyclosporin O Both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP
    • Li, P. & Xu, J.C. (2000) Total synthesis of cyclosporin O Both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP. J. Org. Chem. 65, 2951-2958.
    • (2000) J. Org. Chem. , vol.65 , pp. 2951-2958
    • Li, P.1    Xu, J.C.2
  • 15
    • 0036069515 scopus 로고    scopus 로고
    • A novel N-(Pyrrolidinyl-2-methyl) glycine-based PNA with a strong preference for RNA over DNA
    • Slaitas, A. & Yeheskiely, E. (2002) A novel N-(Pyrrolidinyl-2-methyl) glycine-based PNA with a strong preference for RNA over DNA. Eur. J. Org. Chem. 14, 2391-2399.
    • (2002) Eur. J. Org. Chem. , vol.14 , pp. 2391-2399
    • Slaitas, A.1    Yeheskiely, E.2
  • 16
    • 0002912512 scopus 로고    scopus 로고
    • An approach towards the synthesis of oligomers containing a N-2-hydroxyethylaminomethylphosphonate backbone: A novel PNA analogue
    • Van der Laan, A.C., Strömberg, R., Van Boom, J.H., Kuyl-Yeheskiely, E., Efimov, V.A. & Chakhmakhcheva, O.G. (1996) An approach towards the synthesis of oligomers containing a N-2-hydroxyethylaminomethylphosphonate backbone: A novel PNA analogue. Tetrahedron Lett. 37, 7857-7860.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7857-7860
    • Van der Laan, A.C.1    Strömberg, R.2    Van Boom, J.H.3    Kuyl-Yeheskiely, E.4    Efimov, V.A.5    Chakhmakhcheva, O.G.6
  • 27
    • 0000789462 scopus 로고
    • Peptide synthesis via active esters. IV. Racemization and ring-opening reactions of optically active oxazolones
    • Goodman, M. & Levine, L. (1964) Peptide synthesis via active esters. IV. Racemization and ring-opening reactions of optically active oxazolones. J. Am. Chem. Soc. 86, 2918-2922.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2918-2922
    • Goodman, M.1    Levine, L.2
  • 28
    • 0000277428 scopus 로고    scopus 로고
    • Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis
    • Han, Y., Albericio, F. & Barany, G. (1997) Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J. Org. Chem. 62, 4307-4312.
    • (1997) J. Org. Chem. , vol.62 , pp. 4307-4312
    • Han, Y.1    Albericio, F.2    Barany, G.3
  • 29
    • 0032512076 scopus 로고    scopus 로고
    • Racemization studies of Fmoc-Ser(tBu)-OH during stepwise continuous-flow solid-phase peptide synthesis
    • Di Fenza, A., Tancredi, M., Galoppiini, C. & Rovero, P. (1998) Racemization studies of Fmoc-Ser(tBu)-OH during stepwise continuous-flow solid-phase peptide synthesis. Tetrahedron Lett. 39, 8529-8532.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8529-8532
    • Di Fenza, A.1    Tancredi, M.2    Galoppiini, C.3    Rovero, P.4
  • 30
    • 0033612107 scopus 로고    scopus 로고
    • The diisopropylcarbodiimide/1-hydroxy-7-azabenzotriazole system: Segment coupling and stepwise peptide assembly
    • Carpino, L.A. & El-Faham, A. (1999) The diisopropylcarbodiimide/1-hydroxy-7-azabenzotriazole system: Segment coupling and stepwise peptide assembly. Tetrahedron 55, 6813-6830.
    • (1999) Tetrahedron , vol.55 , pp. 6813-6830
    • Carpino, L.A.1    El-Faham, A.2
  • 31
    • 0034267505 scopus 로고    scopus 로고
    • An improved procedure for N- to C-directed (inverse) solid-phase peptide synthesis
    • Johansson, A., Åkerblom, E., Ersmark, K., Lindeberg, G. & Hallberg, A. (2000) An improved procedure for N- to C-directed (inverse) solid-phase peptide synthesis. J. Comb. Chem. 2, 496-507.
    • (2000) J. Comb. Chem. , vol.2 , pp. 496-507
    • Johansson, A.1    Åkerblom, E.2    Ersmark, K.3    Lindeberg, G.4    Hallberg, A.5
  • 32
    • 0001012518 scopus 로고    scopus 로고
    • Peptide coupling in the presence of highly hindered tertiary amines
    • Carpino, L.A., Ionescu, D. & El-Faham, A. (1996) Peptide coupling in the presence of highly hindered tertiary amines. J. Org. Chem. 61, 2460-2465.
    • (1996) J. Org. Chem. , vol.61 , pp. 2460-2465
    • Carpino, L.A.1    Ionescu, D.2    El-Faham, A.3
  • 35
    • 0005207033 scopus 로고
    • Sulfuranes. II. Isolation and characterization of a crystalline dialkoxydiarylsulfurane
    • Martin, J.C. & Arhart, R.J. (1971) Sulfuranes. II. Isolation and characterization of a crystalline dialkoxydiarylsulfurane. J. Am. Chem. Soc. 93, 2341-2342.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2341-2342
    • Martin, J.C.1    Arhart, R.J.2
  • 36
    • 33947088667 scopus 로고
    • Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers
    • Arhart, R.J. & Martin, J.C. (1972) Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers. J. Am. Chem. Soc. 94, 5003-5010.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5003-5010
    • Arhart, R.J.1    Martin, J.C.2
  • 37
    • 33947088061 scopus 로고
    • Sulfuranes. IX. Sulfuranyl substituent parameters. Substituent effects on the reactivity of dialkoxydiarylsulfuranes in the dehydration of alcohols
    • Kaplan, L.J. & Martin, J.C. (1973) Sulfuranes. IX. Sulfuranyl substituent parameters. Substituent effects on the reactivity of dialkoxydiarylsulfuranes in the dehydration of alcohols. J. Am. Chem. Soc. 95, 793-798.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 793-798
    • Kaplan, L.J.1    Martin, J.C.2
  • 38
    • 33847804765 scopus 로고
    • Sulfuranes. XIV. Single-step syntheses of epoxides and other cyclic ethers by reaction of a diaryldialkoxysulfurane with diols
    • Martin, J.C., Franz, J.A. & Arhart, R.J. (1974) Sulfuranes. XIV. Single-step syntheses of epoxides and other cyclic ethers by reaction of a diaryldialkoxysulfurane with diols. J. Am. Chem. Soc. 96, 4604-4611.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 4604-4611
    • Martin, J.C.1    Franz, J.A.2    Arhart, R.J.3
  • 39
    • 0001721129 scopus 로고
    • Reactions of diaryldialkoxysulfuranes with primary and secondary amines. Preparation and reactions of S,S-diaryl-N-alkylsulfilimines and oxidation of secondary amines to imines
    • Franz, J.A. & Martin, J.C. (1975) Reactions of diaryldialkoxysulfuranes with primary and secondary amines. Preparation and reactions of S,S-diaryl-N-alkylsulfilimines and oxidation of secondary amines to imines. J. Am Chem. Soc. 97, 583-591.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 583-591
    • Franz, J.A.1    Martin, J.C.2
  • 40
    • 0030947731 scopus 로고    scopus 로고
    • Urethane-protected N-carboxyanhydrides (UNCAs) as unique reactants for the study of intrinsic racemization tendencies in peptide synthesis
    • Romoff, T.T. & Goodman, M. (1997) Urethane-protected N-carboxyanhydrides (UNCAs) as unique reactants for the study of intrinsic racemization tendencies in peptide synthesis. J. Peptide Res. 49, 281-292.
    • (1997) J. Peptide Res. , vol.49 , pp. 281-292
    • Romoff, T.T.1    Goodman, M.2
  • 41
    • 0030020427 scopus 로고    scopus 로고
    • Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis
    • Kaiser, T., Nicholson, J.G., Kohlbau, H.J. & Voelter, W. (1996) Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett. 37, 1187-1190.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1187-1190
    • Kaiser, T.1    Nicholson, J.G.2    Kohlbau, H.J.3    Voelter, W.4
  • 42
    • 0033564987 scopus 로고    scopus 로고
    • 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): A new coupling reagent with remarkable resistance to racemization
    • Li, H., Jiang, X. Ye Y., Fan, C., Romoff, T. & Goodman, M. (1999) 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): A new coupling reagent with remarkable resistance to racemization. Org. Lett. 1, 91-93.
    • (1999) Org. Lett. , vol.1 , pp. 91-93
    • Li, H.1    Jiang, X.2    Ye, Y.3    Fan, C.4    Romoff, T.5    Goodman, M.6
  • 43
    • 0000128943 scopus 로고
    • Hydrogen isotope fractionation factors for benzylamine and benzylammonium ion. Comparison of fractionation factors for neutral and positively-charged nitrogen-hydrogen bonds
    • Arrowsmith, C.H., Guo, H.X. & Kresge, A.J. (1994) Hydrogen isotope fractionation factors for benzylamine and benzylammonium ion. Comparison of fractionation factors for neutral and positively-charged nitrogen-hydrogen bonds. J. Am. Chem. Soc. 116, 8890-8894.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8890-8894
    • Arrowsmith, C.H.1    Guo, H.X.2    Kresge, A.J.3
  • 44
    • 84970601917 scopus 로고
    • The basic hydrolysis of amino acid esters
    • Hay, R.W., Porter, L.J. & Morris, P.J. (1966) The basic hydrolysis of amino acid esters. Aust. J. Chem. 19, 1197-1205.
    • (1966) Aust. J. Chem. , vol.19 , pp. 1197-1205
    • Hay, R.W.1    Porter, L.J.2    Morris, P.J.3
  • 45
    • 0001587747 scopus 로고
    • Racemization in peptide synthesis
    • (Gross, E., Meienhofer, J., eds). Academic Press, New York
    • Kemp, D.S. (1979) Racemization in peptide synthesis. In The Peptides (Gross, E., Meienhofer, J., eds), Vol. 1. Academic Press, New York, pp. 315-381.
    • (1979) The Peptides , vol.1 , pp. 315-381
    • Kemp, D.S.1
  • 46
    • 0001420261 scopus 로고
    • Über katalytische racemisation von aminosäuren und peptiden
    • Bergmann, M. & Zervas, L. (1928) Über katalytische Racemisation von Aminosäuren und Peptiden. Biochem. Z. 203, 280-292.
    • (1928) Biochem. Z. , vol.203 , pp. 280-292
    • Bergmann, M.1    Zervas, L.2


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